STR Like The Best

Most 23-year-olds are figuring out their first job. Rajan Chida was turning down JP Morgan to build luxury cabins in Virginia.In this episode, I sit down with Rajan Chida, co-founder of Royal Oak Retreats, to talk about how he went from reselling shoes on eBay in college to developing ground-up luxury STR cabins and building a 550K social media following in under a year.Rajan's story is not your typical real estate success story. It's about stacking capital early, betting on yourself at the right moment, and using social media as leverage in a way that most developers with 10 years of experience still don't understand.We break down:How Rajan funded his first real estate project with shoe reselling money he saved from age 17, and why starting a "job" at 17 gave him a head start most investors don't get until their mid-twentiesWhy his 550K following didn't convert to bookings the way he expected, and the pivot to female travel influencers that finally got Royal Oak Retreats fully bookedThe permitting nightmare in Warren County, Virginia that nearly derailed the entire project, including a disgruntled neighbor, a six-page complaint full of false claims, and a road he had to build just to get the permit approvedHow tariffs forced him to resource his signature window walls from Poland, adding three months of delays and zero construction progressWhy he turned down his JP Morgan offer two weeks before his start date, and the conversation with his dad that gave him the confidence to make that callThe pre-deposit playbook he's using for cabins two and three, including $50 deposits, VIP early access, and how Travis at Outpost X raised $1M before breaking groundThe bottom line: social media is not just a marketing tool. In the hands of the right person, it replaces the track record, the connections, and the credibility that used to take a decade to build.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people think building a successful STR portfolio comes down to markets, numbers, and design. They're missing the one thing that actually makes or breaks everything.In this episode, I sit down with Liz to talk about what has quietly powered every risk we've ever taken, every property we've bought, and every hard moment we've fought through together over the last 10 years.This isn't a real estate tactics episode. It's the one we probably should have recorded sooner.We break down:How Michael's belief in Liz on a subway ride in 2017 led her to quitting her job and going all in on STRWhy mutual belief between spouses is a superpower most people completely overlookThe moment I lost confidence in myself and what Liz said that brought it backWhat our "Corona Battle Plan V2" spreadsheet reminded us about working through the hardest seasons togetherWhy cutting your spouse down to keep them close is one of the most poisonous things you can do in a relationshipHow we divided responsibilities across a 30+ property portfolio so we each lead where we're strongestThe bottom line: If you know your spouse has your back no matter what, you will take bigger risks, make better decisions, and build something neither of you could have built alone.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

There's always a reason not to buy. In 2020 it was COVID. In 2022 it was rising rates. Today it's tariffs, gas prices, and AI uncertainty. The investors who waited are still waiting.In this episode, I sit down with Liz to walk through exactly why we're closing on our eighth short-term rental, a $2.1M property, despite everything happening in the headlines right now.We're not ignoring the noise. We're explaining how we filter it, why the STR tax loophole makes buying now more compelling than ever, and how being a married couple investing together is one of the most underrated advantages in real estate.We break down:Why there's always a reason not to buy, and why waiting has cost investors more than any recessionThe exact data process Liz uses to find underserved markets and identify the right propertyHow the 100-hour rule works as a married couple and why your combined hours are more powerful than you thinkWhy we pushed closing back 10 days on this deal and what the due diligence process actually looks likeThe basis step-up strategy we're using to pass this portfolio to our kids tax-freeWhy the One Big Beautiful Bill has made STR assets more valuable than they were a year agoThe bottom line: uncertainty is permanent. Your tax bill is optional.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most married couples filing jointly have no idea they are sitting on one of the most powerful tax advantages in the entire tax code.In this episode, Michael sits down with co-host Liz to break down exactly how married couples can use the 100-hour material participation rule to qualify for the short-term rental tax loophole, and how they are using it right now across 7 properties with a $2.1 million deal currently in contract.This is not a theoretical conversation. This is exactly what Michael and Liz are doing in real time, with two young kids, multiple properties, and a six-figure tax liability on the line.We break down:What the short-term rental tax loophole actually is and how it allows you to offset W2 income, 1099 income, and capital gains with paper losses from depreciationWhy married couples can combine their hours and how that means one spouse doing 10 hours and the other doing 10 hours counts as 20 hours from a material participation perspectiveThe exact hours Liz has logged in the last 16 days since going under contract on their $2.1 million Tennessee property, including design work, vendor coordination, and mood board creationWhat Michael's day one plan looks like and how he is managing insurance, loans, cleaners, and an operational team before they even close on April 16thHow the post-close launch phase is the easiest way to knock out your hours and why a week on the ground at your property can get you to 100 hours faster than you thinkWhy 100% bonus depreciation is back as of July 2025 and what that means for high-income couples who are ready to stop paying six figures in taxes every single yearThe bottom line: being married is not just a life decision. With the right strategy, it is one of the most powerful tax advantages available to working professionals in America today.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income CouplesMost high-income couples think staying home means giving up financial contribution. They're wrong.In this episode, Michael sits down with co-host Liz to break down why being a stay-at-home parent is one of the most powerful tax strategies available to high-income couples, and how they have used it to save six figures in taxes while building a 30-property portfolio generating $2.3M per year.This is not a conversation about babysitting and diapers. It is about identity, wealth building, and a tax strategy most CPAs never explain correctly.We break down:The 100-hour rule vs. the 750-hour REP requirement and why most people confuse the two, and why that confusion costs them a fortuneHow one spouse staying home creates the perfect material participation setup for the short-term rental tax loophole, even if the other spouse earns seven figuresThe identity guilt that stops smart, driven people from walking away from their careers and how STRs let you keep bothWhy a tax refund is not free money and what to actually look at on your return to understand your real tax burdenHow to hire your kids into the business to compound family wealth and reduce taxes even furtherEstate planning as the next frontier for STR investors who are building a legacy, not just a portfolioThe bottom line: the stay-at-home parent is not the one sacrificing for the family. With the right strategy, they are the one saving it the most money.Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at www.thestrtaxloophole.comLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most investors open AirDNA, look at the numbers, and think they've done their research. They haven't.In this episode, I sit down with my co-host and wife Elizabeth to pull back the curtain on the exact process we use to evaluate STR markets for our clients and ourselves.We've been doing this for 10 years. We've survived the pre-COVID boom, the COVID collapse, and the post-COVID correction. And in that time, we've built a network, a process, and a level of market depth that most investors don't even know exists.We break down:Why AirDNA is a great starting point but will mislead you if you stop there, and how we layer in agent intel, property manager data, and on-the-ground conversations to get the full pictureThe exact questions Liz asks every broker and property manager before recommending a single market to a client, including regulation landscape, price range fit, and occupancy opportunityWhy market selection is the one thing you can't get wrong, and how we've seen first-time investors struggle not because they operated poorly, but because they started in the wrong marketHow Liz has analyzed close to 200 properties in just the first two months of 2025, and why that repetition is what separates real market knowledge from guessworkThe matching process we use to pair high-income clients with the right market for their budget, timeline, and risk tolerance, from $750K inland properties to $1.5M+ beach marketsWhy the work doesn't stop once you find a property, and what it actually takes to go from closing to a fully optimized, revenue-generating STRThe bottom line: anyone can look at data. Very few people know how to read it, layer it, and act on it. That's the difference between guessing and knowing.Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at www.thestrtaxloophole.comLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most STR investors hit a wall around property 3 or 4. Not because they run out of deals, but because conventional lenders start stacking paperwork, haircuts, and restrictions that make it nearly impossible to keep moving.In this episode, I sit down with Robin Simon, author of The Book on DSCR Loans, to break down every financing option available to short-term rental investors and exactly when to use each one.Robin spent years inside the DSCR lending industry, took a year off to write a 715-page book on the subject, and used that same time to buy three STRs himself using the strategies he teaches. This is the conversation I wish I had before I started scaling.We break down:What DSCR loans actually are and how they're different from conventional financing, including why they look at the property instead of your W-2The second home loan trap most new investors fall into, and why the 180-day occupancy rule makes it nearly impossible to cash flowWhy the 5 to 50 property range is the sweet spot for DSCR loans, and when conventional financing still makes more senseHow DSCR loans work with LLCs, partnerships, and trusts, and why serious investors structure it this way from the startThe connection between DSCR loans and the STR tax loophole, and how using both together lets you keep scaling without your tax returns slowing you downWhat Robin learned buying three STRs himself, including the paperwork reality that conventional lenders put high earners throughThe bottom line: the financing tool you choose determines how fast you can scale, and most high earners are using the wrong one.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

You just spent $1M on a property. Now someone is telling you to spend another $200K on design. That fear is real, and it stopped me too.In this episode, I sit down with Jordan McDonough and Bri West, co-founders of Somerled Designs, the largest short-term rental focused design firm in the country, to break down why professional design is the highest-ROI decision you can make for your STR investment.Jordan and Bri have worked with hundreds of STR investors and manage over 35 properties of their own. What they've built at Somerled isn't just a design firm. It's a data-first strategy that tells you exactly what to build, who to build it for, and how to make sure it pays for itself.We break down:Why design is a revenue driver, not an expense, and how to calculate the ROI before you spend a dollarThe data and comp analysis Somerled uses to forecast revenue and build the right design budget for any marketWhy generic design is a losing strategy in 2026 and what "niching down" actually looks like in practiceThe amenity stacking strategy that creates hero shots, drives bookings, and separates top 10% properties from everyone elseWhy relying on Airbnb alone to sell your property is no longer enough and what a real marketing strategy looks likeThe "astrology cabin" case study: how Bri branded a 3-bedroom cabin around a theme guests didn't know they wanted until they saw itThe bottom line: the investors winning in this market aren't spending more. They're spending smarter, and design is where the smartest money goes first.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way.In this episode, I sit down with Hailie Marie, short-term rental operator and angel investor, to talk about how she scaled a 70-unit remote arbitrage portfolio from scratch and why she's now using that cash flow to build long-term wealth.Hailie built something most operators never do: a business that runs without her. Nine VAs, a full tech stack, 24/7 coverage, and AI handling guest communications around the clock. She did it starting with three units in Austin at 19 years old.We break down:How Hailie scaled from 3 units to 70 using arbitrage as a tool, not a destination, and what she's building toward nextThe exact tech stack running her remote portfolio, including HostAway, PriceLabs, TrueV, Bestie AI, Kendo AI, and Phantom AIWhy she uses 9 VAs to run 70 units remotely and how she structured 24/7 coverage without burning out her teamHow AI is training her customer service and cold calling teams in real time, and why she says it improves humans rather than replacing themThe one habit every operator should start now: recording everything, because your future AI tools will need that dataWhy her tax bill was the wake-up call that's pushing her from arbitrage into ownership, and what bonus depreciation changes everythingThe bottom line: Arbitrage can make you cash flow. But the operators who win long-term are the ones using that cash flow to buy assets, build systems, and invest in things that compound.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

What 19 STR Properties Taught Me About Finding Deals Nobody Else Can SeeMost STR investors buy based on what their realtor tells them, what a random listing looks like, or what their gut says. And then they wonder why the numbers never hit the projection.In this episode, I sit down with Jeremy Werden, co-founder of BNBCalc, to break down how data-driven underwriting separates the investors who build real wealth from the ones who just get lucky once.Jeremy started with a $5,600 pontoon boat at 23 years old with no credit and no cash. Today he operates 19 STR listings across multiple states and built one of the most widely used underwriting tools in the industry. This conversation is packed with the kind of hard-won insight you only get from someone who has actually done it at scale.We break down:Why your realtor's projections are almost always wrong and what to use instead to underwrite a property in 25 secondsThe 50-comp framework BNBCalc uses to show you exactly where your property stacks up against the competitionWhy defensibility is the most overlooked factor when buying an STR and the costly Florida mistake that proved itHow to reverse engineer what top operators are doing to find markets and properties with a real edgeWhy the STR tax loophole is only powerful if you buy the right property and hold it for the long termWhat the new BNBCalc markets tool does and why it changes how investors identify opportunities before anyone elseThe bottom line: the investors winning right now are not smarter than you. They just have better data and they know how to use it.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

You bought a great property. You amenitized it. You listed it. And then you priced it with your emotions and left thousands of dollars on the table.In this episode, I sit down with Julie Brinkman, CEO of Beyond Pricing, to break down why revenue management is the most overlooked lever in your STR portfolio and what the top operators are doing differently.Julie has been leading Beyond for almost six years, and the data her team sits on is unlike anything else in the industry. This conversation will change how you think about pricing forever.We break down:Why 55% of STR hosts are using Airbnb smart pricing or nothing at all, and why that's quietly destroying their returnsThe 15 factors Beyond analyzes for every single night of your calendar, and why a spreadsheet can never competeHow Beyond uses guest intent data to see demand shifts before they show up in the marketWhy the booking window collapsed in 2025 and what that means for how you price your calendar right nowWhy last minute discounting is training your guests to wait you out, and what to do insteadWhat private equity consolidation in the STR space means for independent operators in 2026The bottom line: your property is a six-figure asset. It deserves a revenue management system that treats it like one.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

You've built a successful career by outworking and outthinking everyone around you. So why does building wealth outside your W2 feel so hard?In this episode, Michael and Liz sit down to talk about the one thing that actually accelerated their journey from a few properties to a 30+ unit portfolio: community.They share how a corporate "zero-sum" mindset kept them isolated early on, and what changed when they started asking for help, showing up at conferences, and surrounding themselves with people a few steps ahead. This isn't a fluffy conversation about networking. It's a real look at how one introduction, one conversation, or one piece of advice from the right person can unlock years of progress.We break down:How meeting one person at a conference in 2016 led to virtual assistants, better systems, and eventually the entire STR Like The Best education businessThe mindset shift from "figure it out alone" to building a network that compounds over timeWhy high earners often struggle to ask for help and how cultural and personality factors play into itWhat their mentorship community actually looks like with 150+ investors, 20 team members, and resources at every stage from search to operationsThe give-and-take dynamic that attracts the right people and filters out the ones who only takeWhy trying to do this solo is like playing on "super hard mode" and what to do insteadThe bottom line: The fastest path to building wealth isn't figuring it out alone. It's finding the right people who've already done it and learning from them.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Usually we focus on short-term rental investing, tax strategy, and how high-income professionals can offset W2 income through STRs. Today's different. Michael sits down with his college friend Eli Cohen, who's acquired $600 million in multifamily real estate over 15 years, to talk about something every investor needs to understand: knowing when to walk away.In 2022, Eli stopped buying. Not because he ran out of capital. Because the returns didn't justify the risk anymore. This conversation is about market timing, discipline, and deal selection principles that apply whether you're buying your first Airbnb or your tenth apartment building.We break down:Why Eli stopped buying. The Fed said "we no longer have your back." Eli listened and shut down acquisitions. Groups that kept buying are now facing capital calls and wipeouts.The controversial REIT take. Public REITs are cheaper than private multifamily deals right now. You get diversification, liquidity, no promote fees, and better debt costs. "Why would anyone pay more for an illiquid private deal?"When Eli DID buy in 2024. San Francisco off a major REIT, well below pre-COVID pricing. Denver dramatically below seller's cost basis. Both below replacement cost with strong fundamentals.Michael's deal selection story. "I looked at dozens of STR deals. One came up with crappy iPhone photos. We knew it was different. Made an offer the next day. Strong cashflow and appreciation followed. You need the reps to develop conviction."The fast food arbitrage. Operating businesses and real estate trade at different multiples. If you own both, you can shift value between them. Eli's developing chicken restaurants across Texas using this strategy.The power of showing up. Michael drove up with his daughter in a stroller. The sellers were grandparents. They gave her a teddy bear. "That teddy bear is worth a million dollars now."Whether you're buying short-term rentals, multifamily, or restaurants, the principles are the same. Do the reps so you recognize the right deal. Know when the market doesn't justify the risk. Walk away when it doesn't make sense. Move fast with conviction when you see the right one.This isn't your typical STR episode, but the lessons on market timing and deal selection apply to any real estate investor.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people ask us: "Why would you teach this? Why not just keep it to yourself and do more deals?"Fair question.In this episode, Michael and Liz sit down to answer that question and share the real story behind STR Like The Best, the core values that drive everything they do, and why they've helped hundreds of high-income professionals build STR portfolios from scratch.We break down:The $10K/month origin story. How one apartment in Queens making $5,000/month in cashflow while they were both working in investment banking showed them there was a different path than the 9-to-5 grindWhy they started teaching. Friends and family kept asking "how do you do that?" They started sharing online. The community response surprised them. Seeing student success became more rewarding than doing deals themselvesThe transformation stories. From stay-at-home moms launching their first property remotely (Philadelphia to Dallas) to couples quitting their jobs to run 18+ units. The self-confidence people develop is the real winThe four core values that guide every decision: (1) Family first, (2) Long-term thinking, (3) Numbers not feelings, (4) Responsibility to their communityLiz's immigration story. Coming to the US at 16, working in fashion for 9 years, feeling stuck in paycheck-to-paycheck cycles, and only seeing family once a year for one week. The lack of time freedom drove her to real estate meetups every weekMichael's "brainwashed" moment. Investment banking taught him nothing about tax strategy, cost segregation, or building wealth outside of a W2. "We're brainwashed to think we have to work a job till 65 and pay our taxes. But no, there's a different way."The 6 weeks in Taiwan. How they achieved the level of freedom to spend July and August abroad with their kids, something impossible when working in banking, proving location independence is realThe vision for the community. It's not just about buying one property and saving on taxes. It's holistic financial planning: estate planning, insurance, tax-efficient investing for your kids, building generational wealth. Real estate is one piece of the puzzleWhy abundance mindset works. "There's so much opportunity out there. We don't have enough money or time to hit it all. We want to teach you so you can have this for yourself." When you share knowledge, it comes back in unexpected ways (deal flow, partnerships, connections)If you've ever wondered why high-income professionals are leaving stable careers to build STR portfolios, or why hundreds of people trust Michael and Liz to guide them through this strategy, this episode gives you the unfiltered answer.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

If you're manually responding to guest messages at 11pm, you're competing with one hand tied behind your back.In this episode, Michael sits down with Annie, co-founder of HelloHost (the AI platform Michael uses in his own STR business), to break down how AI is fundamentally changing short-term rental operations and why hosts who don't adapt will get left behind by operators who are 10x more efficient.We break down:How Airbnb is reading every message you send with AI to enforce policies, detect guest problems, and make decisions about review removals, whether you know it or notWhy Michael went from highly skeptical to running his entire company on HelloHost in 2-3 weeks (started with 3 lowest-performing listings, now uses it for all 30+ properties)The multi-agent system that makes 90% automation possible. It's not just a chatbot, it's multiple AI agents debating in real-time to get the answer right before respondingWally, the operations AI agent that lives in your WhatsApp/Slack and handles maintenance coordination, guest info lookups, and mass messaging ("Hey Wally, tell all my guests Merry Christmas")How ChatGPT is becoming a discovery platform and why Airbnb's negotiating with OpenAI over who controls the booking flow (and what this means for your listings)Why AI costs are subsidized right now and won't stay cheap. The Uber pricing trajectory from $2 rides in 2010 to $45 for 10 minutes todayAI Engine Optimization (AEO): The new SEO for getting your property discovered on ChatGPT and LLMs, not just GoogleWhy review removal is now AI-assisted and the default answer is "no." Understanding how platform decisions are being automatedAI is not coming to short-term rentals. It's already here. Airbnb is using it. Your competition is using it. Michael uses HelloHost for all 30+ of his properties because if you're not using AI to handle guest communications and operations, you're working 10x harder for the same results. The subsidized learning period is now. Costs will go up dramatically in the next few years.Try HelloHost free for 30 days at strlikethebest.com/hellohostLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most couples can't work together without wanting to kill each other. Add two kids under five, 30+ properties across multiple states, and a seven-figure business to the mix, and you've got a recipe for disaster.Except it's not.In this episode, Michael and Liz pull back the curtain on how they actually make it work. Not the Instagram highlight reel. The real stuff. The 2:30 AM wake-ups, the fights they avoided by hiring smart, the one rule that's saved their marriage, and why making more money solved more problems than therapy ever could.We break down:The one non-negotiable rule about how they talk about each other (in public and private) that's kept their partnership strongWhy "you can't manage what you can't measure" applies to marriage just as much as business, and the KPIs they actually trackHow they built the business before kids and why that timing gave them an unfair advantage when babies arrivedThe delegation framework that works for both business and home (virtual assistants, cleaners, postpartum nannies, and why there's no pride in doing dishes)Why Liz was pregnant for 12 of the last 60 months and how they structured support during postpartum recovery (hint: it wasn't just "tough it out")The mindset shift from "no one can do it like me" to trusting a global team of 20+ people they've never met in personHow making more money isn't about working more, it's about hiring out everything you're not good at or don't want to doWhy working with your spouse means no operating agreements, no distribution fights, no tax headaches, just two people rowing in the same directionThe transferable strengths they've borrowed from each other (EQ, design thinking, analytical skills) and how they've covered each other's weaknessesBeing married and working together is either your biggest asset or your biggest liability. The difference comes down to alignment, delegation, and one critical rule about how you treat each other when things get hard.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

If you're only on Airbnb, you don't have a business. You're a vendor to Airbnb. And if they change the algorithm, spike their fees, or suspend your account over a bad review, your entire income disappears overnight.In this episode, Michael sits down with Shaun Shirazian, CEO of Lodgify, to break down why property management systems are non-negotiable for anyone serious about STR investing, how the right tech stack creates three types of independence, and why AI is about to fundamentally change how small operators compete.We break down:The three types of independence STR investing unlocks (financial, location, and time) and why diversification across OTAs is the only real protection against platform riskWhy 86% of hosts have 7 listings or below, and why software built for 100-unit operators doesn't work for the long-tail marketHow Lodgify helps hosts go from Airbnb-only to multi-channel distribution with a direct booking website in minutes, not weeksThe mental model shift from managing one OTA to managing a real business through a PMS system, and why the calendar is the most important visual elementAI's role in guest messaging (90% automation is now possible with tools like HelloHost) and why pricing optimization is the next frontier no one has solved yetWhy properties with just one distribution channel struggle to fill weekdays, and how multi-platform presence dramatically lifts occupancy ratesTechnology is just the how. The what hasn't changed in 20 years. Hosts want passive income, peace of mind, and independence. The right tech stack makes that possible. The wrong one (or no tech stack) keeps you trapped.Try Lodgify free at www.lodgify.comFor direct questions, email Shaun at [email protected] MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Your CPA says you make too much money. They say you work too many hours at your job. They say you need to be a real estate professional. All three of those statements are wrong.In this episode, Michael sits down with Amanda Han and Matt MacFarland from Keystone CPA, two of the leading tax experts in the short-term rental space, to break down exactly how the STR tax loophole works, why most CPAs get it wrong, and how to protect yourself if the IRS ever comes knocking.We break down:The three material participation tests that actually matter (500 hours, 100 hours with no one else having more, and more hours than everyone combined) and why married couples have a major advantageThe grouping election that most CPAs miss entirely because it's a paragraph, not a form, and why this one oversight can destroy your audit defense when you scale to multiple propertiesWhat actually counts toward your hours (hint: it starts when you go under contract) and what doesn't count no matter how much time you spend on itA real IRS audit case study where the auditor automatically disallowed all losses because the properties were out of state, and how it ended with zero changes after proper documentationWhy properties with lower land value create significantly larger tax benefits and which markets give you the best depreciation potentialThe three red flags that signal your CPA does not understand the STR loophole (if you hear any of these, it's time to find a new accountant)Best practices for documentation including RepsTracker, separate phone systems, dedicated email addresses, and why showing up as an "A plus student" changes everything in an auditWith bonus depreciation now permanent at 100%, this is the most meaningful window for high-income W2 earners to legally offset substantial income through short-term rental investing. But only if you do it right.Check out Keystone CPA: https://strlikethebest.com/keystonecpaFollow Amanda on Instagram: https://www.instagram.com/amanda_han_cpaLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

LEARN HOW I ANALYZE IF A PROPERTY WILL WORK AS A STR 🔥 https://strlikethebest.com/strlitmustest?utm_source=podYou're about to wire $150K for a down payment based on a revenue projection. But three different platforms just gave you three different numbers. Which one is real?In this episode, Michael sits down with Jae Seok An, founder of AirBtics and former Meta software developer, to pull back the curtain on how short-term rental data actually gets built and more importantly, how to know if the numbers you're betting your money on are accurate or fantasy.We break down:The review-matching verification method that reveals when a property claiming 80% occupancy only has two reviews (the simple check sophisticated investors use before trusting any data)Why scraped data can actually be more comprehensive than first-party PMS data, and the real tradeoffs between accuracy and coverage that most investors don't understandHow 36 months of historical data reveals seasonality issues and bad comps that annual snapshots completely miss (this is why monthly breakdowns matter more than you think)The technical truth behind how platforms collect, process, and present your numbers, from data scrapers to cleaning algorithms to the alerts that catch when things go wrongWhy averaging three different data points guarantees you the wrong answer, and what to do instead when platforms give conflicting projectionsData confidence is the difference between taking action on great deals and second-guessing yourself into paralysis. When you understand how the numbers actually get made, you can finally trust your analysis enough to pull the trigger.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

USE MY 5-STEP LITMUS TEST TO SEE THE PROFITABILITY OF A POTENTIAL PROPERTY: https://strlikethebest.com/litmuspodQ4 2025 Market Update: What's Actually Working Right NowMost people think high-income professionals are buying Airbnbs for cash flow. They're wrong.In this episode, Michael and Liz reveal the real reason why employees at Meta, Amazon, Blackstone, and Goldman Sachs are aggressively buying $750K-$1.5M short-term rental properties and it has everything to do with the tax code.We break down:How to legally offset $300K+ in W2 income with a single property purchase (and why paying 40% in taxes is optional if you know what you're doing)The markets actually producing results in 2025 (Tennessee, Colorado, Pennsylvania) and which expensive Northeast markets are complete trapsA real $2M property case study where the owner is leaving $50K+ on the table annually through basic pricing mistakes (this happens more than you think)Why this only works as a long-term hold strategy, and why trying to flip your way through this will get you destroyed by the IRSThe difference between markets with "good regulation" versus those that will make your investment impossible to operateThe bottom line: If you're making $200K-$650K in W2 income, taxes are your biggest expense, bigger than your mortgage, bigger than anything else. This episode shows you exactly how to turn that expense into your biggest wealth accelerator.This is what they don't teach you in business school.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

LEARN MY STR INVESTING & STRATEGIES 🔥 https://coaching.strlikethebest.com/7figureexit?utm_source=ytPart 4 — Taipei SeriesPart 3 explored how mentorship, consistency, and STR tax strategy turned business growth into leverage and legacy. Part 4 dives into how those same principles shape parenting, raising kids with judgment, integrity, and emotional intelligence in an AI-driven world.1. From business lessons to family values, why reputation, patience, and presence matter more than rules.2. Teaching likability, empathy, and good manners as early superpowers for building lifelong relationships.3. Building trust and teamwork between siblings, how shared responsibility, family rituals, and environment compound character.Apply to work with Michael: https://strlikethebest.com/applyytFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthytPart 3 — Taipei SeriesEpisode 2 showed how humility, metrics, and defined roles turned conflict into scale, systems + a global team protecting marriage and ROI; Episode 3: dives into building our media/education engine (mentors, consistency) and how STR tax strategy (incl. 100% bonus depreciation) lets high-earners buy cash-flowing assets and cut taxes.Episode Highlights:1. From zero followers to a global brand—how mentorship and daily consistency fueled growth.2. Turning STR experience into education, helping high-income earners build wealth and save six figures in taxes.3. The roadmap ahead, community growth, elite vs. concierge programs, and future events + fund vision.Apply to work with Michael: https://strlikethebest.com/applyytFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthytPart 2 — Taipei SeriesIn the previous episode, Michael and Liz shared how systems, tech, and a global team let them run ~40 STRs remotely. In this part of the series, they continue the conversation, diving into how they work together as a married team, balance decision-making with data, and turn early conflicts into a scalable structure.Episode Highlights:1. Offloading guest comms to a global team + PMS/AI to remove emotion and reclaim focus2. Switching from per-bedroom to whole-unit stays for better ops, guest experience, and profits3. Respecting strengths (design vs. finance), 80/20 time management, and hiring A-playersThey end this episode on how mutual respect and structured delegation strengthen both the business and the marriage, teeing up Part 3 on scaling the media and education side of their brand.Apply to work with Michael: https://strlikethebest.com/applyytFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthytFrom Taipei, Michael and Liz show how systems, tech, and a global team let them run ~40 STRs remotely, reclaim family time, and help clients save taxes while scaling. Episode Highlights:1. Hands-off weekly hours, kids immersed with family and mandarin2. Staff across 5 continents and working collectively to run 95% of business operation3. The renewed 100% bonus depreciation spiking client deals. They close on why sharing their playbook grows an abundance-minded network and tee up the next episode on exactly how they split roles and keep the machine smooth.Apply to work with Michael: https://strlikethebest.com/applyytFollow Michael on Instagram:   / michaelchangbnb  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

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 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

In this episode of STR Like the Best, I sit down with Alex Alioto, Co-Founder and Head of Growth at Whimstay, an OTA built specifically to fill your last-minute and gap-night inventory.We break down why relying solely on Airbnb is like owning a stock portfolio with just one stock, how to think strategically about OTA distribution, and why last-minute travelers aren’t just bargain hunters—they’re a fast-growing segment that can boost your weekday occupancy.Alex shares practical tips on integrating with Whimstay, avoiding the “race to the bottom” on pricing, and meeting the needs of the next-gen traveler (21–35 year olds booking 8–10 trips a year). We also talk about the importance of focusing on what is working in your business, and the role gratitude and key relationships play in the journey.Whether you’re looking to maximize revenue, diversify your booking channels, or simply reframe your mindset as an operator, this episode delivers both tactical strategies and a reminder to enjoy the people you meet along the way.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

In this episode, I sit down with JJ King—STR operator, ex-product lead, and serial entrepreneur—who scaled from answering Craigslist ads to running a 300-unit property management company. We dive deep into the early rental arbitrage days in NYC, how a cold outreach strategy turned into a SaaS acquisition, and what it takes to scale a property business sustainably in today’s market. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

In this week's episode, Michael Chang and Avery Carl, CEO of The Short-Term Shop, break down the brutal reality of today’s short-term rental market and why that’s exactly where the opportunity lies. If you want to thrive in today's market and position yourself for outsized returns, this episode is a must-listen.Subscribe for more STR investor strategies every week.JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES https://www.strlikethebest.com/insider⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted✅ Follow Michael http://www.instagram.com/michaelchangbnb ✅ Follow Avery http://www.instagram.com/@TheAveryCarl   LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥 https://www.strlikethebest.com/insiderIn this episode, Michael Chang and Philip Kennard discuss the evolving landscape of short-term rentals, focusing on the importance of direct bookings versus relying solely on online travel agencies (OTAs) like Airbnb. They explore the benefits and challenges of both strategies, emphasizing the need for rentalpreneurs to build trust with guests, manage payments effectively, and implement marketing strategies to capture direct bookings.In this conversation, Michael Chang and Philip from FutureStay also discuss the importance of SEO and direct bookings for property managers, the role of Google Vacation Rentals, and the value proposition of FutureStay as a high-converting website solution. They delve into the new Airbnb policies, their implications for hosts, and the supportive nature of the hospitality community. Tune in to get all the details!🤑Get my free Airbnb Launch Guide by joining 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted✅ Follow Michael http://www.instagram.com/michaelchangbnb🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥 https://www.strlikethebest.com/insiderIn this episode of STR Like the Best, Michael Chang sits down with Jeff Illoulian, CEO of HostGPO, to explore how short-term rental operators can save money and streamline their furnishing process.Jeff shares his journey from managing 150 STR units to founding HostGPO, a group purchasing organization offering discounted, hospitality-grade furniture, linens, and amenities.They dive into the operational mistakes many hosts make, the importance of commercial-grade supplies, and how HostGPO helps elevate the quality and profitability of STR businesses.🤑Get my free Airbnb Launch Guide by joining 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted✅ Follow Michael http://www.instagram.com/michaelchangbnb🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥 https://www.strlikethebest.com/insider⭐ In this conversation, Michael Chang interviews William Lucas, the chairman of Mint House, a leading company in corporate housing and short-term rentals. William shares his entrepreneurial journey, the inception of Mint House, and the challenges & strategies involved in raising capital and building a scalable team. ⭐ They highlight the importance of technology in hospitality, the need for a strong brand in the short-term rental market, and the significance of hiring the right people to drive business success. ⭐ The discussion also covers the decision-making process between buying properties versus managing them, and Will shares insights from his transition to a chairman role. ⭐ The episode concludes with reflections on future STR opportunities and the importance of mentorship in entrepreneurship. 🤑Get my free Airbnb Launch Guide by joining 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider   In this episode, I sit down with Sarah and Emily — better known as the Karwells — two best friends turned powerhouse STR investors who’ve raised over $5.5 million from everyday investors, built a thriving portfolio of uniquely designed Airbnbs, and launched a brand that spans education, e-commerce, retreats, and more.  We talk about how they evolved from scrappy designers working for free to learn the game… to running a full-fledged STR operation that prioritizes community, creativity, and transparency.  Whether you're an aspiring host, capital raiser, or someone building a brand in this space — this episode will show you what’s possible when you combine heart, hustle, and high standards.  What You’ll Learn: How the Karwells raised $5.5M+ in equity capital for STR deals  Why design, hospitality, and investor trust are their edge  How they balance friendship and business (and why it actually makes them stronger)  The power of community and building in public  What makes a deal worth doing — and what they say “no” to  Their expansion into e-commerce and retreats, and how it's all connected  The importance of honest underwriting (and why most deals don’t pencil)  Chapters: 00:00 – Introduction and Personal Reflections 00:13 – Introducing the Guests: the Karwells 01:38 – the Karwells' Journey into Short-Term Rentals 03:27 – Building a Business and Partnership 09:56 – Evolving the Business and New Ventures 22:26 – The Importance of Community and Networking 27:11 – Reflecting on Financial Growth 27:19 – Understanding Wealth and Short-Term Rentals 28:18 – The Importance of Transparency with Investors 28:42 – Celebrating Fundraising Milestones 29:27 – Design and Hospitality in Property Management 31:32 – The Value of Honest Underwriting 34:53 – Launching Retreats for Networking and Education 40:04 – Finding the Right Deals and Investors 45:51 – The Power of Community and Generosity 51:39 – Closing Thoughts and Contact Information Follow The Karwells on Instagram → @thekarwells  Learn more about their upcoming retreats → thekarwells.space LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

In this episode, Michael Chang and Thomas Castelli, CPA, break down essential tax strategies for short-term rental investors. Learn how to leverage the "short-term rental tax loophole" to offset W-2 income, maximize depreciation benefits, and avoid common tax pitfalls. They also discuss material participation rules, bookkeeping best practices, and key deductions to optimize your financial outcomes. Don't miss these expert insights to grow your wealth through smart tax planning! 🚀JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted✅ Follow Michael http://www.instagram.com/michaelchangbnb🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=ytIn this episode, the host discusses the principle of not letting tax benefits dictate investment decisions with Thomas Castelli. The conversation focuses on ensuring that property investments make sense financially on their own rather than being driven by potential tax depreciation. The discussion also touches on the complexities and time commitments involved in managing properties, especially when one does not live in proximity to them. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, host Michael Chang interviews Federico Zimmerman, a seasoned property manager operating a short-term rental management company with 65 properties across 12 states in the U.S. Federico shares his inspirational journey of transitioning from a corporate career in Argentina to starting and scaling a successful short-term rental business in the United States. He highlights the challenges and key decisions involved in building his business, the importance of networking, and the complexities of managing multiple properties remotely. This episode provides valuable insights for aspiring property managers and anyone looking to optimize their short-term rental operations.  CHAPTERS:00:00 Introduction and Career Reflections00:21 Welcoming Federico Zimmerman01:38 Federico's Journey in Short-Term Rentals05:17 Challenges and Growth in Property Management11:34 The Leap to the United States20:53 Starting Over and Building Success24:59 Strategic Growth and Partnerships30:14 Building Your Business Through Relationships30:51 Strategic Property Management31:54 Managing Properties Across States33:46 Operational Challenges and Solutions35:12 The Importance of a Strong Team37:21 Client and Guest Expectations40:47 The Value of Property Management45:56 Learning from Mistakes and Moving Forward51:13 The People Behind the Business52:59 Final Thoughts and Reflections  ⬇️ Apply to work with Mehttps://www.strlikethebest.com/getstarted ✅ Follow Michaelhttp://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d📖 Join 6,000+ Investors on our STR Investing Newsletterhttps://www.strlikethebest.com/subscribe?utm_source=yt #Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, Michael Chang interviews Pierre-Camille Hamada, CEO of hospitable.com, discussing the transformative impact of AI technology on short-term rental management. Pierre shares his unique journey from a law career to founding a leading property management software, emphasizing the importance of automation and technology in enhancing guest experiences and streamlining operations for hosts. The conversation explores the current landscape of property management systems, the underserved market of small hosts, and the critical balance between distribution and automation in maximizing rental business efficiency⬇️ Apply to work with Mehttps://www.strlikethebest.com/getstarted ✅ Follow Michaelhttp://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletterhttps://www.strlikethebest.com/subscribe?utm_source=yt LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 02:54 Understanding the Value of Cost Segregation 06:03 The Role of CPAs in Real Estate Investing 08:55 Short-Term Rentals and Tax Benefits 14:45 The Future of Cost Segregation and Legislative Changes 17:57 Real-Life Examples and Case Studies 20:47 When Cost Segregation May Not Be Beneficial 24:06 The Importance of Control in Real Estate Investing⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb ✅ Get Your RE Cost Seg https://get.recostseg.com/strlikethebest 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d📖 Join 6,000+ Investors on our STR Investing Newsletter:https://www.strlikethebest.com/subscribe?utm_source=yt LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, Michael Chang interviews Jonathan Farber, a successful real estate investor and entrepreneur. Jonathan shares his journey from a sales software company to building a diverse real estate portfolio, including short-term rentals. He discusses creative financing strategies, the shift to short-term rentals during COVID, and the importance of market dynamics in real estate investing.  00:00 Intro to Jonathan’s journey03:09 Portfolio overview05:54 Creative financing09:03 Short-term rental shift14:56 Navigating regulations17:55 Differentiating in the market21:10 Future business focus27:55 Virtual assistants31:32 Building routines and goals ⬇️ Apply to work with Me  https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb ✅ Follow Jonathan https://www.instagram.com/jonjfarb/ ✅ Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of STR Like the Best, Michael Chang sits down with Shahar Goldboim, CEO of Boom AI, to explore how artificial intelligence is reshaping the way short term rental hosts and property managers operate.From centralizing tasks to boosting efficiency and increasing revenue, Shahar shares the innovative strategies behind Boom AI.Shahar also opens up about his journey of scaling a property management business, the importance of building a great team, and how technology can address some of the toughest challenges in the short-term rental industry.Episode Highlights:00:00 Building a Winning Team00:21 Introduction to Property Management Systems01:06 Guest Introduction: Shahar Goldblum02:51 The Importance of a Centralized PMS05:21 Scaling with a PMS: A Personal Story12:02 AI Integration in Property Management22:24 Revolutionizing Customer Support with AI24:03 Challenges in the Property Management Industry31:05 The Power of Networking and MentorshipIf you’re looking for practical insights on scaling your Airbnb business with smart tools and strategies, this episode is for you. 🎧 Tune in now!⬇️ Apply to work with Mehttps://www.strlikethebest.com/getstarted ✅ Follow Michaelhttp://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify:https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d📖 Join 6,000+ Investors on our STR Investing Newsletterhttps://www.strlikethebest.com/subscribe?utm_source=yt LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of STR Like The Best, Michael Chang sits down with leading hospitality entrepreneur Isaac French to discuss thriving in the ever-evolving short-term rental market.Michael and Isaac dive into the dynamics of scaling a traditional rental business versus crafting unique accommodations, and what investors should know in order to strike the right balance between these two strategies.⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted✅ Follow Michael / http://www.instagram.com/michaelchangbnb✅ Follow Isaac /  http://www.instagram.com//isaacfrench_ 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt#Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of STR Like The Best, host Michael Chang sits down with industry expert Caleb Shore to reveal strategies for scaling your short-term rental business in the evolving landscape of 2025 and beyond.Tune in to learn how to:- Leverage advanced revenue management to maximize profits.- Master effective hiring techniques for building a strong team, even in tough markets.- Utilize virtual assistants to streamline and expand your operations.- Tap into emerging markets like Charlotte, North Carolina, for growth opportunities. Turn local insights into a competitive edge in a global industry.- Whether you're starting out or aiming to scale up, this episode offers valuable insights to help you stay ahead in the short-term rental game. Key Moments:00:00 The Hiring Mistake That Changed Everything00:19 – Introduction: Scaling in 2025 & Beyond01:22 – Caleb's Vision for the Future of STR Business04:55 – Revenue Management: Your Secret Weapon11:45 – Innovative Business Models for Scalability17:59 – Leveraging Local Knowledge Globally22:43 – Effective Hiring Strategies for Modern Challenges34:25 – Conclusion: Your Roadmap to Success 📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe🏡 Start and make money with STR Arbitrage💰 Build long-term wealth with STR Investing⚙️ Earn back your precious time with STR automations LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider  Today, I'm thrilled to be joined by STR Like The Best coaching member Jaime Cabal! In less than a year after joining the program, Jaime has scaled his Airbnb business into a thriving global operation and investment portfolio. He’ll be sharing the strategies, pivotal decisions, and insights that fueled his rapid success in the short-term rental industry 00:00 Introduction to Jaime Cabal's Journey 02:16 Launching the Airbnb Business in Miami 06:43 Managing Airbnb Units Remotely10:40 Transitioning to Property Management in Madrid 19:39 Investing in Real Estate and Building a Portfolio25:34 The Importance of Relationships in Business Watch more on Youtube: https://www.youtube.com/@michaelchangbnb?sub_confirmation=1 LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of 'STR Like The Best,' host Michael Chang interviews seasoned investor Michael McKay about advanced real estate negotiation strategies and the evolution from Airbnb to property flipping. They discuss McKay's focus on solving sellers' problems, his business model in Jacksonville, Florida, and the significance of knowing oneself in business. The conversation covers marketing strategies, short-term rental insights, unique renovations, and adapting to market changes. Key takeaways include understanding seller motivations, building a competent sales team, and leveraging local regulations for competitive advantage. The episode concludes with advice on networking and securing sales jobs in real estate, emphasizing mentorship and the impact of strategic connections. 00:00 Introduction to Real Estate Negotiation 00:24 Meet Michael McKay: From Airbnb to Real Estate Flipping 01:12 Michael McKay's Journey in Real Estate 02:21 Transition to Jacksonville and Real Estate Strategy 06:13 Building a Real Estate Business in Jacksonville 08:58 Direct to Seller Acquisitions and Flipping Strategy 19:29 Success Stories and Unique Deals 23:48 Sales Staff and Hiring Plans 24:26 Impact of Market Changes on Real Estate 26:56 Shift from Institutional to Retail Buyers28:16 Adapting to Market Conditions32:01 Lessons from Short-Term Rental Investments 35:54 Unique Property Features for Success 45:03 Networking and Mentorship in Real Estate 48:35 Conclusion and Contact InformationFollow Michael Mckay On Socials..Instagram: https://www.instagram.com/mike_mckayYouTube: https://www.youtube.com/channel/UC3Aqb0ex_lWuJ-3wdsBPUtg LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, host Michael Chang engages with guest Chewy, a seasoned short-term rental entrepreneur, discussing pathways to success in the Airbnb market.They cover Chewy's journey from commercial real estate to short-term rentals, leveraging word of mouth for podcast growth, and the power of social media in forming valuable connections.Chewy shares his experiences of starting out in Shanghai, applying lessons from arbitrage, and managing 25 rental units several years later.They also tackle challenges such as copyright issues and the benefits of partnership in entrepreneurship.The episode concludes with insights into the importance of taking calculated risks and maintaining an abundance mindset for continued success.00:00 Introduction and Podcast Growth00:21 Welcoming Chewy and Initial Conversation01:49 Chewy's Background and Journey to Real Estate02:55 First Experience with Arbitrage06:51 Learning from Courses and Finding a Business Partner14:34 Challenges and Growth in Arbitrage18:31 Balancing Vacation and Business Rentals20:48 Navigating Business Partnerships22:11 The Importance of Trust in Business25:36 Dealing with Legal Challenges29:37 The Value of Solving Problems with Money34:30 Building a Supportive Community37:26 The Power of Generosity in BusinessFollow Chewy On Socials.. Instagram: https://www.instagram.com/chewyyylFacebook. Group: https://www.facebook.com/groups/airbnbhostshelpinghosts📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, Michael Chang and Simon Lehmann, the the leaders in the short-term rental industry, share insights on the evolution of the industry, the impact of COVID-19, the role of technology, and the challenges faced by major OTAs.The conversation delves into the challenges and the future outlook of the industry. It also explores the importance of unit density, market localization, and the balance between centralized and decentralized operations.00:00 Evolution of the Short-Term Rental Industry08:04 Impact of COVID-19 on Market Penetration12:06 Challenges and Opportunities for Major OTAs24:13 Navigating the Short-Term Rental Industry: Challenges and Opportunities31:42 The Role of Technology and Economies of Scale in Property Management35:30 Unit Density and Market Localization: Driving Sales Tax Returns40:53 Balancing Centralized and Decentralized Operations in Property Management43:27 The Future Outlook for the Short-Term Rental IndustryConnect with Simon on LinkedIn: https://www.linkedin.com/in/simon-lehmann-8375753b/ 📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter: https://www.strlikethebest.com/subscribe?utm_source=yt #vacationrental #airbnb #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbbusiness #airbnbinvesting LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider  In this episode, host Michael Chang welcomes Ann Marie Folan, a real estate broker at Douglas Elliman, to discuss her journey from being a real estate attorney to a successful real estate broker and investor in Manhattan and the Hamptons. They explore Ann Marie's strategies for real estate investments, including the short-term rental market, and delve into her personal story of how she leverages property investment to build substantial equity. Ann Marie also shares insights into her operational approach, managing multiple properties, and instilling entrepreneurial skills and resilience in her daughter. The episode highlights the significance of equity building, property management, and the multifaceted aspects of successful real estate investment. 00:00 Introduction and Podcast Growth00:26 Guest Introduction: Ann Marie Folan01:24 Anne Marie's Real Estate Journey02:10 Manhattan Real Estate Insights04:23 Success in the Hamptons08:23 First Hamptons Property Purchase16:00 Diverse Perspectives in Real Estate16:33 Optimizing for Equity Over Cash Flow16:47 House Number Two: A Case Study19:02 Managing Multiple Properties23:36 The Third House: A New Venture26:59 Teaching the Next Generation32:34 Concluding Thoughts and Contact Information 📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt  🏡 Start and make money with STR Arbitrage💰 Build long-term wealth with STR Investing⚙️ Earn back your precious time with STR automations LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, host Michael Chang welcomes Sam Dundas, co-founder of Besty Ai, to discuss the transformative role of AI in the short-term rental industry. They explore how Besty Ai enhances guest communication, automates tasks, optimizes operations, and drives revenue growth for property managers. The conversation covers Sam's journey from property management to AI, the economic implications of AI adoption, potential risks, and how AI can democratize efficiency gains for both large and small operators. The episode also delves into the future of AI in rental management, emphasizing the importance of adopting AI tools to stay competitive.00:00 Introduction and Podcast Growth00:26 Welcoming the Guest: Sam Dundas01:21 Sam Dundas' Journey into Property Management02:22 Transition to Software and Founding Besty Ai03:27 Strategies for Short-Term Rental Investing08:30 The Role of Virtual Assistants in Property Management12:53 Introduction to Besty Ai19:19 AI in Property Management: Benefits and Challenges20:53 Future of AI in Short-Term Rentals29:17 Understanding AI Reasoning Engines29:41 The Importance of Prompting in AI29:47 How AI Handles Guest Questions30:31 Processing Layers in AI Responses31:29 Economics of AI in Business32:04 Sustainability and Cost of AI32:34 AI Models and Efficiency34:51 Future of AI and Cost Reduction37:30 Risks and Challenges in AI Implementation39:30 Impact of AI on Management Fees40:41 AI in Property Management46:49 Investor Considerations in AI49:52 Conclusion and Future OutlookCheck out Besty Ai today https://www.instagram.com/getbestyai/  📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode, Michael Chang and Sean Rakidzich share their insights on scaling an Airbnb arbitrage business. They discuss the benefits of arbitrage over buying properties, emphasizing immediate cash flow and rapid expansion.Sean also talks about the challenges of scaling, the significance of core values, and future growth opportunities in distressed multifamily properties.00:00 Introduction and Background06:15 Current Portfolio and Business Strategy09:12 Choosing Arbitrage over Buying Properties12:30 Benefits of Arbitrage and Cash Flow19:17 Scaling the Business and Lessons Learned41:12 Hiring the Right People46:20 Future Growth Opportunities Follow Sean Rakidzich on Youtube https://www.youtube.com/@AirbnbAutomated 📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of STR Like The Best, host Michael Chang interviews Zach Edelman, a Senior Account Executive at Easy Street Capital.Zach shares his expertise in STR lending, specifically on DSCR loans, which are ideal for short-term rental investors. He discusses the nuances of DSCR loans, their advantages over conventional loans, and his journey from underwriting to a front-facing sales role.This episode is essential for anyone interested in the financial aspects of short-term rental investments and looking to understand the intricacies of DSCR loans.00:03 Introduction to Zach Edelman and Easy Street Capital04:12 What are DSCR Loans?06:06 DSCR Loans vs. Conventional Loans07:50 Loan Pricing and Costs Explained09:45 Current Market Rates and Trends12:27 Zach's Professional Journey and Underwriting Experience15:02 Underwriting and Loan Structuring18:45 Key Advice for Borrowers32:15 Market Insights: Hot and Cooling Markets35:26 Loan-to-Value Ratios and Unlocking EquityConnect with Zach Edelman:Instagram: @ZachEdelmanESCEmail: [email protected]📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt 💰What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz 💰 Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4 💰Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of STR Like The Best, host Michael Chang interviews Gil Chan, the CEO and founder of Crafted Stays, who shares his journey from a tech background to becoming a successful short-term rental investor & entrepreneur.Gil's company helps hosts build polished websites and strategic marketing plans to drive more direct bookings. They also delve into practical tools and tactics for collecting emails, effective marketing campaigns, and leveraging social media for better ROI.This episode is a comprehensive guide for STR hosts looking to optimize their business and reduce OTA dependency. 00:54 Gil's Background and Journey into Short-Term Rentals01:43 First Property and Learning Curve03:35 Tax Benefits of Short-Term Rentals08:27 Leveraging Technology and Tools19:32 Optimizing and Expanding the Portfolio24:31 Designing and Marketing for Your Target Audience28:19 Building a Direct Booking Strategy29:31 Balancing Direct Bookings and OTA Platforms35:35 Crafting a Professional Direct Booking Website 39:12 Effective Marketing Tactics for Direct Bookings48:13 Conclusion and Final Thoughts📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscr... 🏡 Start and make money with STR Arbitrage💰 Build long-term wealth with STR Investing⚙️ Earn back your precious time with STR automations ---------------------------------------------------------------------------------------------------------- What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz - Spotify Podcast: https://open.spotify.com/show/141mIvb... - Apple Podcast: https://podcasts.apple.com/us/podcast... #airbnbinvesting #realestateinvestor #airbnb #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider In this episode of 'STR Like the Best,' host Michael Chang welcomes Kenny Bedwell, CEO and founder of STR Insights. They discuss the importance of data analysis for growing a short-term rental business.Kenny shares his personal journey from a corporate professional to owning multiple short-term rental properties. He offers insights on the best high-ROI amenities, the significance of understanding guest avatar, and practical tips for using data to make informed investment decisions.00:26 Guest Introduction: Kenny Bedwell03:18 First Short-Term Rental Experience & Challenges08:19 How to Underwrite Short Term Rental Investment Property10:38 Portfolio Management and Strategy27:40 STR Insights: Market Planning Tool31:28 Understanding Gross ROI and Market Selection35:33 Cash on Cash Return vs. Cash Flow39:34 Operational Efficiency and Automation46:26 Evaluating Property Upgrades and Amenities52:12 Data Integrity and Decision MakingFollow Kenny Bedwell on Instagram: https://www.instagram.com/kenny_bedwell/ 📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt 🏡 Start and make money with STR Arbitrage 💰 Build long-term wealth with STR Investing⚙️ Earn back your precious time with STR automations--------------------------------------------------------------------------------------------------------- - -- What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz - Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4 - Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369  LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/